1. Field of the Invention
This invention relates to (i) 5-aroyl-6-chloro-(or bromo)1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-caboxylic acids and the pharmaceutically acceptable, non-toxic alkyl esters and salts thereof; (ii) the use of these compounds as anti-inflammatory agents, analgesic agents, platelet aggregation inhibitors, fibrinolytic agents and smooth muscle relaxants (this includes both prophylactic and therapeutic use); (iii) pharmaceutical compositions comprising a compound of this invention and at least one pharmaceutical excipient; and (iv) processes for preparing the compounds of this invention.
2. Prior Art
Compounds are known which are represented by the formula ##STR2## wherein P is a moiety selected from the group consisting of ##STR3## in which X is oxygen or sulfur,
R is hydrogen, methyl, chloro or bromo, the R substitution being at the 3, 4 or 5 positions of the thiophene ring, PA1 R.sup.1 is hydrogen, a lower alkyl group having 1 to 4 carbon atoms, a lower alkoxy group having from 1 to 4 carbon atoms, chloro, fluoro or bromo, the R.sup.1 substitution being at the ortho, meta or para positions of the phenyl group, and PA1 R.sup.2 and R.sup.3 are each independently hydrogen or a lower alkyl group having from 1 to 4 carbon atoms. PA1 Y is chloro or bromo and PA1 Ar is a radical represented by the formula ##STR5## in which X is sulfur or oxygen;
The compounds represented by Formula (IA) and (ID) are disclosed in U.S. Pat. No. 4,087,539, issued May 2, 1978 to Muchowski, et al while compounds of Formulas (IB) and (IC) are disclosed in U.S. Pat. No. 4,089,969, issued May 16, 1978 to Muchowski et al and U.S. Pat. No. 4,097,579 issued June 27, 1978 to Muchowski et al, respectively.
Compounds of Formula (IB) wherein R.sup.1 is methylthio are disclosed in copending U.S. application Ser. No. 71,444 filed Aug. 31, 1979, now abandoned and compounds wherein R.sup.1 is methylsulfinyl or methylsulfonyl are disclosed in U.S. Pat. No. 4,232,038, issued Nov. 4, 1980. All of these compounds are useful as antiinflammatory agents, analgesic agents, platelet aggregation inhibitors, fibrinolytic agents and smooth muscle relaxants. They can be used both prophylactically and therapeutically.